Sodium Hydroxide → (4-Tert-butoxycarbonylphenyl)(hydroxy)phenylacetic acid

HRID 1058294Notes

Reaction equation

HRID 1058294 reaction equation
C([O:3][C:4](=[O:26])[C:5]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:15][CH:14]=1)([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[C:22]([O:21][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:5]([OH:12])([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:4]([OH:26])=[O:3])=[CH:14][CH:15]=1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 69939053Ethyl(4-tert-butyloxycarbonylphenyl)(hydroxy)phenylacetate

Product 1

HCID 69939119(4-Tert-butoxycarbonylphenyl)(hydroxy)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl(4-tert-butyloxycarbonylphenyl)(hydroxy)phenylacetate from the previous step (78 mg, 0.218 mmol, HPLC RT=2.95 min.) in 2 mL CH3OH was added 0.3 mL of 1 N NaOH solution. Reaction was stirred at room temperature for 4 hours. HPLC analysis indicated rapid conversion to methyl ester but slow saponification to acid. Added 0.1 mL 1 N NaOH to drive reaction to completion. The solvent was removed on a rotary evaporator and the residue was partitioned between EtOAc (20 mL) and 1 N HCl (5 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed on a rotary evaporator. (4-tert-butoxycarbonylphenyl)(hydroxy)phenylacetic acid was obtained as a white solid. (62 mg, 87%); HPLC RT=2.53 min, method B. 1H NMR, 400 MHz, DMSO-d6, 13.4 ppm (br s, 1H); 7.85 ppm (d, J=7.5 Hz, 2H); 7.50 ppm (d, J=7.32 Hz, 2H); 7.34 ppm (m, 5H); and 1.53 ppm (s, 9H).

Workup

  1. customReaction
  2. customreaction to completion
  3. customThe solvent was removed on a rotary evaporator
  4. customthe residue was partitioned between EtOAc (20 mL) and 1 N HCl (5 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-1f38b61468a747b59fd5aed46d345e99
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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